Welcome back to The Digital Workplace podcast. Today our very special guest is Phil Simon. Phil is the award winning author of “Reimagining Collaboration.” Hey, Phil. How’s it going today?

Neil, thanks for having me.

It’s great to connect with you. We got connected and within about three minutes of a phone call of all things I realized this is a brother. This is somebody who thinks deeply about this stuff, and we want to hear from you. So I’m so excited to have you on the show and to learn more about you.

Too high for me, man, in just getting to the point, say this guy’s average or mediocre and then, oh, you know what? He’s actually better than anticipated. You don’t want a par the first two holes on a golf course, you’ll get nowhere to go but down.

Alright, alright, fine. You may hate this podcast. That’s all right. But first, Phil, we got to always check. I don’t like talking to robots on the show. So we got to check. Are you a real life human? Your CAPTCHA question is I want you to share with us your favorite Wordle starting word.

System error. I’m kidding. I am human. I have switched over to crane, but I used to start with atone. Because as an avid scrabble person, I know that you are knocking off a lot of them. I didn’t like adieu. I know a lot of people went there. I like to be systematic about it. But then I think sometimes that’s boring. So I’ve been going with crane. And I think today when we recorded I think I nailed it on the fourth turn.

By your Twitter feed, that’s correct, the fourth turn.

Someone follows me on the Twitter, lookout stalker.

Well, cool. Alright, that qualifies. My word is teams. I like that, of all things.

Fun fact, not to criticize, but evidently, the way it’s programmed, from what I’ve read, nothing ends in S. Steam might be a better one. But they wouldn’t have words four letters plus an S because I think it just expands it too much. So you may want to try steam. But there may be a benefit to doing that. I don’t want to be too technical about it because I like the serendipity. But that’s a good choice.

I’m switching. Steam is the new one.

That was easy. A lot easier than getting us together, man.

It’s true. It’s true. For all the listeners out there, this took too long and too many mistakes on my side. Being in the real world, I didn’t estimate on travel times and stuff. I got to stick to digital places. It’s much easier.

Plus I filled out the form on the website. Was it six months ago and it went to your spam or something?

Yeah.

So there’s that. This better be good, man. There’s been a lot of build up to this. You’ve got to bring your A game, Neil.

So speaking of the build up, you wrote a book. You wrote many books. Tell us about “Reimagining Collaboration,” how you got there, and why you wrote it.

Sure. I was writing “Zoom for Dummies” in a furious pace to meet an aggressive deadline. I was able to bang through that 400-page book pretty quickly because it actually had a lot in common with Slack. And then I started using Microsoft Teams with my publisher. So there was this new breed of powerful collaboration tools that obviated a great deal of email and back and forth. But most people would look at Zoom as Skype 2.0 or Slack or Teams as email 2.0. I understand it. Many companies don’t invest in training. It wasn’t necessarily someone’s job to write a 400-page book about Slack or Microsoft Teams or Zoom. But they were much more powerful than people had realized. I want to say that it was Toni Morrison who said if the book you want to read doesn’t exist, then you have to be the one to write it. So far be it for me to argue with OG Toni Morrison, but I did.

Excellent. I read the book, listened to the book, actually. But it was fascinating. And I feel like there’s a lot of good things about it. We’re going to unpack a lot of things all about collaboration, how we’re doing it. Let’s go back to what I’ll call the beginning of this digital influence. We’re going to with email. So tell me your thoughts about the role that email played circa 1990 in organizations.

We go back three decades that it played an indispensable role. Internal, external, I mean, I’m old enough to remember sending letters to friends, not that there’s anything wrong with that today, kind of miss it, nostalgic or internally going back to the I wasn’t around for the 60s. I’m not that old. But I have watched Mad Men so you’d get intra office memos that could get lost.

In the envelope, right? The manila.

Yeah, the envelopes. In fact, in the mid 90s, for one of my internships, there was email, you would type out a letter and printer. Then WordPerfect, that was the big deal. I remember printing something out and it wasn’t WYSIWYG, gosh, I’m dating myself, in 1993 and being so frustrated that what I thought I was getting on the screen wasn’t what ultimately came out of the printer. So, yeah, email remains an essential tool. But I keep using golf analogies. Let’s use a different one. If you only have a hammer, you think everything’s a nail. So particularly for internal communication, I’ve been ranting about email for years, even in 2015, I wrote a book called “Message Not Received” about why business communication fails and TLDR, as the kids say, way too much jargon, way too much email. So if you’re going to replace email with another tool, the question becomes what and then the tools, back when I wrote that book, are nothing compared to the contemporary, what I’ll call internal collaboration hubs that exist today.

Let’s break down. Where does email fail? I think most of the people that are listening to this understand the issues of email, but let’s just make sure everyone’s on the same page of why, internally, email is a bad system. And we’ll get into more of how you should use email. But first, what’s your case? Quick, why should we stop using email internally?

We get too many of them. Back in 2015, I discovered that the average corporate employer received about 120 emails per day, and the rate was growing at around 15% per year. So that would effectively double in four and a half years. People check their inboxes something like every seven or eight minutes, and even when they get the message, they don’t necessarily understand it. There was an interesting study I cited in that book from a guy named Nicholas Epsy. I believe he was out of University of Illinois, about how when you send someone a message, only 46% of the time could you detect if the person was using humor. That’s an interesting stat.

I remember around that time, one of my favorite bands, they’re very obscure, they’re called Marillion. I’ve gotten to know some of the members of them and see them in concert and even went on a run once with the keyboardist Mark Kelly. When I was interviewing him for Huffington Post, he said, “Could we talk about your book for a minute?” I said, “You guys are 1000 times more interesting, but twist my arm, sure.” And he explained the story about how, and this band’s been together since the early 80s, going on four decades now, there was this misunderstanding with the drummer over email, and they finally got him in a room and said, “Dude, what’s wrong?” And he goes, “What are you talking about?” So if you’ve been working with people for over 30 years, and you misunderstand each other, what does that say about people who have been working with each other for 30 days or 30 months?

Apart from that, and this is where the collaboration hubs that are discussed in “Reimagining Collaboration” really shine, Neil, your inbox and all the content in it effectively dies the minute that you leave a company. So let’s say that you are the head of marketing, and you leave for greener pastures. You move your family, whatever. Well, all of the communication, all the knowledge, all the documents, all the decisions go poof. Now, occasionally, yes, an IT person can resurrect a key message because it contains a file or whatever. But there’s a lot of friction in that. So if we use, say, Slack, which is my favorite internal collaboration hub, then I’m deactivated, but all my information is still there. So if I made an interesting comment, or sent a document and posted it there, then if you’re the new head of marketing, you can see, oh, yeah, this is what Phil had created, that starting point versus trying to recreate it.

Or subsequent to my new book coming out, I saw the Asana Anatomy of Work index dropped in April of 2021, and something like in the United States, employees spend around 31% of their day on what they call work about work. In other words, scheduling, which you and I know well. I’m trying to find a document or recreating a different document or just doing frustrating administrative stuff. Well, I’m not saying that if something is in Slack, you’ll find it instantly. But there are much more powerful tools. Plus, there’s a permanence to it. Plus, we can segment conversations. Again, I can use Outlook and Gmail rules for folders and tags and all that and that’s all fine and dandy, but let’s just say, and then there are companies that do this. I’m a big music fan. There is a dedicated channel to just riff on music. Could you imagine getting an email from someone, Neil, going, Hey, I like this band. Why are you bothering me? Go away.

But if you’re in a channel, it’s a lot more informal. In fact, Marshall McLuhan famously said, the medium is the message. So the minute that you get an email from your boss you tense up. Now you could still be tense if you get that DM in Slack, or someone posts a message in a channel in Microsoft Teams. But there’s more transparency as well, I can, if I join a company, see what’s going on in the company at my own speed. If I join an organization and HR sends me 72 emails with forms, have to fill out, immediately I’m overwhelmed and tense.

Other than that, though, I’m not anti-email. You and I initially connected over email, but again, with our scheduling issues today, I sent you a note going, dude, call me, and then we were able to work it out a lot quicker. So I’m not anti-email. I’m anti-inefficiency. And this notion that Slack or Teams or Zoom is just email or Skype is absurd. It’s like saying my Lexus convertible is a coffee cup holder. Well, it’ll do that. I don’t have a Lexus convertible. But that’s a joke from Gary Gulman. Your car actually does a few more things than hold your coffee mug.

Yeah, I find that a lot of people who push back against the email, one, it’s just the familiarity. That’s just what they’re used to. You also have those people who are the email wizards out there. They have 60 filters set up that everything goes through and they say, “Hey, I’ve spent years of my life getting this the way I wanted to. It works for me. I want to keep it that way.” Then you have the other people who say, “Yeah, I’ve tried Slack. It’s just like email just faster. And it’s all the same. We still have misunderstandings. We still get too many messages that come through. I still didn’t getting training on it. It’s like the worst thing.” So how do you take those into account and address those issues?

I mean, people hate change. The management theorist Peter Singer famously said, “People hate change unless it’s their idea.” So I would counter that even though you may be good at something, you’re not only emailing yourself. In fact, why would you really do that? You can, but why would you? You’re communicating or collaborating with others. In Chapter 2 of “Reimagining Collaboration,” I thought that it was essential for me to define collaboration against a number of adjacent terms, because we typically conflate them. If I’m communicating, I’m making something common. That’s all communication is. If I’m collaborating, I’m working with someone to get something done. That’s different than productivity. I could be productive by myself. It’s different than project management. It’s different than coordination.

So I’d say that it’s essential for people to think more broadly. It’s not just about you and works for you. If you don’t like that, then guess what? Sometimes you have to make changes. The workplace isn’t a democracy. I was just reading a fascinating protocol article about how I guess some designer signed up to work for a company. He parenthetically asked, “What do you guys use internally for collaboration?” And they said Microsoft Teams. The guy said, “You know what? I can’t take the job. I’m a Slack person.” I think we actually may wind up seeing more than that, because if the organization only communicates exclusively by email, and more and more folks are using these tools, will they want to revert? I mean, Microsoft announced that there were 300 million active monthly Teams users. Slack had peaked at 15 million. I think that that pretty much stayed still. But this notion that I need to be constantly in my inbox, getting a message from anyone in the world about anything at any time, just doesn’t hold up anymore. It is much easier. You’re a Slack fan, right?

Yeah, I mean, I use Slack, but I will say I like Slack for a specific purpose. I actually like Slack more outside of work for communities that I’m a part of. Whether that be my neighborhood or a group of people I like to connect with, I find it to be most useful for that. I’ve actually found that I don’t like Slack as a communication hub, which let’s get into this term, because you used this idea of you need a hub for all the collaboration that happens, and then you have spokes run that. Flush that out, just in a quick two minute explanation.

Yeah. Again, many people equate Slack or Teams to email 2.0, or Zoom to Skype 2.0. Then there’s Google Workspace and Facebook/Meta’s, what do they call it? Workplace, it’s so hard to keep them all on track. So in the book, I argue that all of your communication and collaboration only take place there. Period. That’s tremendously valuable because it solves all the problems that email causes. But then hubs really become powerful when you connect them with these third party apps. You can use Slack to the fullest extent possible. Slack is not an enterprise resource planning system, like Workday. It’s not a document signature tool, like Docusign. It’s not a productivity tool per se, like Microsoft Office or Google Docs. So you can connect those third party apps, or what I call spokes, to the main hubs and create this single Gestalt. So I can consolidate all of my notifications in one place. If someone updates a ticket in Zendesk, I don’t have to go to my email, or launch a separate Zendesk app or webpage. It lets me know there.

Now, again, Slack or Teams or any of the other hubs will not make third party apps unnecessary. But if you can connect them in a more cohesive way, then you’re not multitasking as much. You’re not frustrated by all these notifications from different applications. You don’t have to be terribly technical to do it. If you can install an app on your phone, you can install the Google Docs or Google Drive or Workspace, whatever they’re calling it these days, app for Slack. So when I’m collaborating with someone in a Google Doc and someone comments, I don’t get an email. I get a notification in Slack. I’ve got that context. I could see that comment right then and there. So there are ways. I still get email. That’s how we connected. So email becomes less frequent, less universal, and hopefully, you’re getting fewer of them and they mean more. But we are just scratching the surface when it comes to what these hubs can do. Again, to my knowledge, there was no book out there that explored them. So I do feel like in the sea of books on the future of work and hybrid and remote work, I like to think that I’ve written a reasonably interesting and distinct text that contributes to this important body of work.

Yeah. So let’s break this down a little bit. The hub is, by your definition, I’m saying it’s where you basically get your notifications. It’s where everything circles back to, right? There’s one thing in the center. Is that fair?

Notifications, but you can also post documents, you could run polls. I mean, again, Slack is so much more than just email. But even in Zoom, you can install third party apps on Zoom. So let’s say that we were brainstorming on something, we want to dial up a whiteboard. We don’t have to go to a separate app. We can do that right in Zoom. If I’m managing a project, if I’m taking notes, if I’m checking off things to do in a productivity app, like Todoist, you can all use those things independently or you could use them through the hub. So imagine a place that you go for almost your digital headquarters. That’s what Stewart Butterfield of Slack has termed the tool. But whether you’re using Slack or Zoom or Teams or some of the other tools that I mentioned, you’re using it in a much more cohesive way than just, oh, this is where I send messages. This is where you could upload files. You can conduct polls. You can even, I hate the term workflow, but Slack has this tool called workflow builder. I could effectively launch a ticket. If I am in Slack is an IT channel, I say my computer doesn’t work. That, within Slack, you could start a ticket off that goes to their ticket management system. So again, it’s not just for communication and collaboration. It can do so much more. So that’s what I think about with a hub. It’s more general use than just this is a messaging tool. It’s not WhatsApp or Snap or whatever else the kids are using these days.

So in, let’s just say, the ’90s or so, email became that hub. It became the thing that everyone was plugged into. Now, I do agree that Slack is a better hub than that. I feel like we pushed email too far. We tried to make it do too many things. We tried to make it come on, and it failed on that. Like you said, it’s a great tool for third party, like I don’t know this person, but let me send them an email type conversations. My question for you is, looking towards the future, is, let’s just take Slack, we’ll just pick on Slack. We can be talking about anything. But is Slack still going to be something we’re going to be proud that we put in the center? Or do we need to think before we make that the hub and not the spoke itself?

To say, for me, let me explain. Chat is great. But chat is often contextless. When somebody sends you a message, it could be about anything, as opposed to a project management tool. If you get a notification about something, you know it’s assigned to a task, it’s assigned to a bigger project that’s going to be there. So the problems I’ve had with having Slack as a hub in my experience is that it’s a similar feel to email where I don’t, I mean, at least it’s in the work world. It’s not email, it could be about anything, at least it’s work. That’s great. I like that. But it could still be about anything. I find if I’m having that as my center, that it’s still distracting. It still feels like a lot of chaos. It still feels like a lot of things going on. It makes me want to put something else in the center and make chat a spoke and make something else the hub. What do you think about that?

It is conceivable that you could use a tool in a way that I don’t think is necessarily optimal, but there’s no way to guarantee that someone is providing the right context. Going back to that music channel example, if I want by accident or by design posted, hey, Neil, you need to do this right now. Slack isn’t going to kick that out right now. Maybe down the road, when there’s more AI and machine learning built in, go, well, dude, you might want to actually move this to a more appropriate place because the music channel might be something that people visit infrequently, or when they want to kill some time, as opposed to a more important one regarding things that you want to do.

Yeah, I mean, look, they’re complements. They’re not substitutes. I don’t believe that Slack or Teams or Zoom will ever be a proper project management application. But if I’m using Asana, if I’m using Trello, if I’m using Basecamp, I can have all those notifications filtered in plus there are limited things that I can do within them. So if someone assigns me a task in Trello, I might mark it as completed without having to go to Trello. I just can do something through a shortcode or something in Slack. So I mean, no tool is perfect. People use them. I could fax you an inappropriate photo. I could send you in the mail. Use your imagination. We like to demonize the tools because the tools can’t yell at us back. It’s very, I think, facile to blame tech. I think many organizations are hoping that employees will pick this up on their own time.

I mean, I’ve even had people complain about my Slack and Zoom for Dummies books, saying, dude, how do you write a 400-page book about this? Well, if you’re only using 2% of the functionality, then yeah, it’s going to seem like overkill. But I’d also argue you should be, if you’re going to be buying the book, you should be willing to learn. And many times people aren’t. So I guess that I’m a contrarian. I mean, even smart cookies like Cal Newport, I’m sure you’ve heard of him.

Yeah, of course.

Yeah. He’s a smart guy. I read “Deep Work,” but in his new book, “A World Without Email,” he effectively equates Slack to email. And it’s because, due respect, he doesn’t understand it. I can customize my notifications by channel, by person, by time, by date, by application, by keyword. Can email do that?

Yeah, I would say Slack is better than email. But I feel like Slack will have the same problems that email will in the sense of, like I said, we pushed email so far that it ended up breaking. We saw all the cracks in it, and it went through that. I feel like we’re going to do the same to Slack. We’re going to push it so far. We’re going to say, I want to do this, I’m going to do this, I’m going to do this, and we’re just going to keep asking for more out of it. Then eventually, you’ll start seeing those cracks and it’ll break. I’m not saying that there’s a better solution. Maybe it’s just, and it’s not Slack’s fault. Maybe it’s how we’re approaching it.

Yeah, I think where we may differ is that I don’t look for a single solution. I mean, I’m a big believer in, as I said, picking up the phone, because you and I were having a hard time with the scheduling. Now, that’s a microcosm. If we were to work together on a regular basis, we’d figure out a way to do it. When people say I don’t want to use Slack or Teams or whatever, I say, at any given point, I have five of these things open because different people have got different communication skills. Now that happens to work for me because I’m an independent. But if I worked at a company, the company really should pick a lane and stick in it. It doesn’t scale particularly well if an organization uses seven hubs. Now there are tools like Mio that can stitch them together.

But it’s, going back to my analogy before with a hammer and a nail, I don’t think that one tool can do everything. There is a time and place for us to talk or to get together, if that’s possible barring lockdown. It’s a lot harder to excoriate someone after you’ve had broken bread with them. If I played a round of golf with you or went to a concert, oh, yeah, he’s a cool guy, versus he’s a Slack or Microsoft Team’s avatar. Who is this guy? I mean, look, I have had people in my consulting days tear me a new one on email who are sitting in a cubicle next to me. I’d stand up and go, “Dude, you just copied the entire world calling me a such and such. What is it?”

So any tool is only as good as the culture. I mean, in “Reimagining Collaboration,” I tell the story of a way the direct-to-consumer luggage company and their CEO, I forget her name, but I think she’s actually married to Slack CEO Stewart Butterfield, used to use the tool as a cudgel. You need to respond at 2 in the morning. I don’t want any private messages sent or private channels. And was quite frankly, very difficult. I can think of a few other words, but I won’t use them. You can be rude or inappropriate using any tool. But no, no tool, including Slack or any of the other ones I discuss in the book, doesn’t prevent someone from being, I’ll just say, a jerk.

Sure. Do you feel like, when it comes to collaboration especially, you did a good job of defining the different, like you said, the umbrella of terms that comes under these things. A message, let’s just talk about one unit of work. So one unit of work is a message. I’ll send you a thing. It comes to you. A notification could be another unit of work. But then we also have things like an event. So a moment in time is also a part of work. A task is a unit of work. As you look towards the future of collaboration, do you think, and this is like, we do reviews of products, we looked at some project management tools that try to treat everything in the world as a task. That breaks down after a while. Same with, I feel like Slack would, not consciously, but it seems like everything is treated as a ping or a message or a unit of text that’s there. When you look at the future of collaboration and how things will be built out, what are some of these other units of work that need to be accounted for as we think about a really better collaboration system?

Yeah, well, I think you make an important distinction, Neil. You’ve got regular, what I’ll call, continuing work versus more project work. And yes, to your point, projects can break down into phases, or for using Agile methods like Scrum into Sprint’s Fibonacci numbers or if you use lean methods. So work is a general term. I’m with you. At a high level, though, I’d argue that there are two types. So let’s say that you work in customer relations and you answer phones all day. You’re not really working on a project. I should know because I spent a year at Sony Electronics after college having people scream at me on the phone because their camcorders, and if your listeners don’t know what a camcorder is, look it up. It’s before iPhones. Didn’t work and it was their daughter’s third birthday, and how dare I not have a replacement ready for them tomorrow. And I’m trying to explain what’s going on. It was an interesting year. But that’s not a project. I wasn’t really in any, I think I was in two meetings at Sony in a year. I never worked on a project.

Now, if COVID happens, and I take my calls at home, while I might have an English bulldog barking in the background, or a child running around, or the neighbors doing landscaping, but I can do my job in theory anywhere with internet connection, because it’s really not a project. You can still do projects remotely. Automattic, the company behind WordPress, Basecamp, GitLab. Darren Murph has actually been in my own podcast, absolute rockstar, love that guy. You are talking about building something. That, I think, underscores the importance of hybrid work. I know a lot of people like to dunk on hybrid work as a bandaid. But I don’t think of hybrid work as a binary. You might need to get together to kick off a project or for employee orientation or to just get together in bond. So the office is already starting to change. The idea, though, that you never see your employees, I think would be difficult in any circumstance, particularly if you’re doing something new and we haven’t established the rules of engagement.

I mean, even, I’m no expert on Scrum, but I’ve managed projects using it, and I used to be a college professor teaching it, you’ve got objectivity involved. People skills, still — I’m sorry, subjectivity involved. You still have judgment calls to make. Well, I think this project is going to take two weeks or this user story or this task. So I don’t know if we can be as black and white as saying everything ultimately breaks down into a task, because then you have subtasks, and meetings about tasks. But I do think that these tools can help alleviate a lot of the problems that have plagued us. We were never particularly good at project management or completing tasks in the real world. Then COVID happens, and all of a sudden, you have a hard time finding a common place to meet or you misunderstand something because I don’t pick up on the body language, even in Zoom, it’s not 100% clear, or your Wi Fi goes down or whatever.

So yeah, I mean, the world of work is a complicated one. But I would argue that let’s start by maybe distinguishing what we’re trying to accomplish because of routine tasks. And they can be challenging as well. It’s fundamentally different than following a new process to build something new, especially if you’re dealing with new employees and uncertainty and you haven’t met them before. So these tools can help, but again, they’re not a panacea.

Definitely. There’s so much to unpack here. Phil, you’re the kind of guy I want to come to whenever I have a problem. And it’s like, I don’t…

Oh, gosh. Heaven help you.

And I don’t expect you to solve it. I expect you to make it just more gray almost, like to see, yeah, there’s this side and there’s this side. So I really appreciate what you’ve done. The book is amazing. If people want to check it out, where should they go?

Pretty much anywhere. It’s, I’m sure, in certain bookstores, but it’s easiest to purchase on bookshop.org or Amazon or whatever, Kobo, Apple Books, Google Books, whatever.

All the places, it’s there. Excellent. Phil, it’s been great to have you on. We look forward to collaborating again in the future. Thanks for being flexible with scheduling and everything else. We look forward to connecting with you again.

Thank you, Neil. I enjoyed it. Thank you.